1-Butanol → HCID 44180966, compound

HRID 1042038Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([C:8]2[C:12]3[O:13][C:14]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[CH:15][C:16](=[O:17])[C:11]=3[S:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.N1C=CN=C1.F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[CH2:47]([OH:51])[CH2:48][CH2:49][CH3:50].N12CCCN=C1CCCCC2.[O:63]1CCC[CH2:64]1>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo].CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC(O)=O.CC(O)=O.[Pd].[Pd]>[O:21]1[CH2:22][CH2:23][N:18]([C:14]2[O:13][C:12]3[C:8]([C:4]4[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=4)[C:64]([O:51][CH2:47][CH2:48][CH2:49][CH3:50])=[O:63])=[CH:9][S:10][C:11]=3[C:16](=[O:17])[CH:15]=2)[CH2:19][CH2:20]1

Participants

Conditions

Temperature: 170 °C

Procedure

A 2 mL microwave vial was charged with a magnetic stirring bar, 3-(3-chlorophenyl)-5-morpholino-7H-thieno[3,2-b]pyran-7-one (85) (80 mg, 230 μmol), imidazole (47 mg, 690 μmol), molybdenum hexacarbonyl (60 mg, 230 umol), trans-di(μ-acetato)bis[o-(di-o-tolyl-phosphino)benzyl]dipalladium (II) (6.5 mg, 6.9 μmol), tri-tert-butylphosphonium tetrafluoroborate (4.0 mg, 13.9 μmol), tetrahydrofuran (500 μL), n-butanol (63 μL, 690 μmol), and 1,8-diazabicyclo[5.4.0]undec-7-ene (103 μL, 690 μmol). The vial was immediately sealed, and the reaction mixture was magnetically stirred and heated via microwave irradiation to 170° C. for 15 minutes in a microwave reactor to give butyl 3-(5-morpholino-7-oxo-7H-thieno[3,2-b]pyran-3-yl)benzoate (75).

Workup

additionA 2 mL microwave vial was charged with a magnetic stirring bar
customThe vial was immediately sealed

Sources & evidence

ORD record: ord-3087360e35fe46ed9bb2089b093cfc92
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557807B2

Reaction notes

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